紫精化合物的合成与应用研究进展
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摘要
紫精化合物(viologens)是一类具有独特变色性质的缺电子体阳离子化合物,在变色材料、超分子器件和有机电池等方面有着潜在的应用前景。可通过取代反应设计合成具有不同取代基的紫精,实现性能调控。本文对近年来紫精化合物的合成方法与应用研究进展进行了综述,重点介绍了其在变色、发光等性能方面的潜在应用。
Viologens is a kind of electron-deficient dication(V~(2+)) with characteristic chromatism property. Its unique properties make it potentially useful in electrochromic and photochromic materials, supramolecular devices, and organic batteries. In addition, viologens with different substituents are easily synthesized by substitution reaction to achieve performance tuning. This article mainly introduces the synthetic strategies and recent research progress of viologens, especially its applications in chromic and photo materials.
Viologens is a kind of electron-deficient dication(V~(2+)) with characteristic chromatism property. Its unique properties make it potentially useful in electrochromic and photochromic materials, supramolecular devices, and organic batteries. In addition, viologens with different substituents are easily synthesized by substitution reaction to achieve performance tuning. This article mainly introduces the synthetic strategies and recent research progress of viologens, especially its applications in chromic and photo materials.
引文
[1] WEIDEL H,RUSSO M.Studien über das Pyridin[J].Monatshefte für Chemie/Chemical Monthly,1882,3(1):850-885.
[2] MICHAELIS L,HILL E S.The viologen indicators[J].The Journal of General Physiology,1933,16(6):859-873.
[3] ALESANCO Y,VINUALES A,CABANERO G,et al.Colorless-to-black/gray electrochromic devices based on single 1-alkyl-1′-aryl asymmetric viologen-modified monolayered electrodes[J].Advanced Optical Materials,2017,5(8):1600989.
[4] KAN W Q,WEN S Z,HE Y C,et al.Viologen-based photochromic coordination polymers for inkless and erasable prints[J].Inorganic Chemistry,2017,56(24):14926-14935.
[5] SONG Y F,HUANG X H,HUA H J,et al.The synthesis of a rigid conjugated viologen and its cucurbituril pseudorotaxanes[J].Dyes and Pigments,2017,137:229-235.
[6] LIU T B,WEI X L,NIE Z M,et al.A Total organic aqueous redox flow battery employing a low cost and sustainable methyl viologen anolyte and 4-HO-TEMPO catholyte[J].Advanced Energy Materials,2016,6 (3):1501449.
[7] NANASAWA M,MIWA M,HIRAI M,et al.Synthesis of viologens with extended π-conjugation and their photochromic behavior on near-IR absorption[J].The Journal of Organic Chemistry,2000,65(2):593-495.
[8] CHEN G J,ZHOU Y,WANG X C,et al.Construction of porous cationic frameworks by crosslinking polyhedral oligomeric silsesquioxane units with N-heterocyclic linkers[J].Scientific Reports,2015,5:11236.
[9] DAS G,PRAKASAM T,NURYYEVA S,et al.Multifunctional redox-tuned viologen-based covalent organic polymers[J].Journal of Materials Chemistry A,2016,4 (40):15361-15369.
[10] Lü Z P,CHEN B,WANG H Y,et al.Charge-transfer supra-amphiphiles built by water-soluble tetrathiafulvalenes and viologen-containing amphiphiles:Supramolecular nanoassemblies with modifiable dimensions[J].Small,2015,11(29):3597-3605.
[11] ABOUELWAFA A S,MEREACRE V,BALABAN T S,et al.Photo- and thermally-enhanced charge separation in supramolecular viologen-hexacyanoferrate complexes[J].Crystengcomm,2010,12(1):94-99.
[12] SHI W,XING F F,BAI Y L,et al.High sensitivity viologen for a facile and versatile sensor of base an solvent polarity in solution and solid state in air atmosphere[J].ACS Applied Materials & Interfaces,2015,7(26):14493-14500.
[13] PARK S,KO H C,PAIK W,et al.Assignments of cyclic voltammetric peaks during electrochemical polymerization of pyrrole with viologen pendant[J].Synthetic Metals,2003,139(2):439-443.
[14] CHEN L,WILLCOCK H,WEDGE C J,et al.Efficient access to conjugated 4,4′-bipyridinium oligomers using the Zincke reaction:Synthesis,spectroscopic and electrochemical properties[J].Organic & Biomolecular Chemistry,2016,14(3):980-988.
[15] DURBEN S,BAUMGARTNER T.3,7-Diazadibenzophosphole oxide:A phosphorus-bridged viologen analogue with significantly lowered reduction threshold[J].Angewandte Chemie-International Edition,2011,50(34):7948-7952.
[16] WOODWARD A N,KOLESAR J M,HALL S R,et al.Thiazolothiazole fluorophores exhibiting strong fluorescence and viologen-like reversible electrochromism[J].Journal of the American Chemical Society,2017,139(25):8467-8473.
[17] MORTIMER R J.Electrochromic materials[J].Chemical Society Reviews,1997,26(3):147-156.
[18] BIRD C L,KUHN A T.Electrochemistry of the viologens[J].Chemical Society Reviews,1981,10(1):49-82.
[19] SYDAM R,GHOSH A,DEEPA M.Enhanced electrochromic write-erase efficiency ofa device with a novel viologen:1,1′-Bis(2-(1H-indol-3-yl)ethyl)-4,4′-bipyridinium diperchlorate[J].Organic Electronics,2015,17:33-43.
[20] PAN M J,KE Y L,MA L,et al.Single-layer electrochromic device based on hydroxyalkyl viologens with large contrast and high coloration efficiency[J].Electrochimica Acta,2018,266:395-403.
[21] ALESANCO Y,VINUALES A,PALENZUELA J,et al.Multicolor electrochromics:Rainbow-like devices[J].ACS Applied Materials & Interfaces,2016,8(23):14795-14801.
[22] LIN R G,XU G,WANG M S,et al.Improved photochromic properties on viologen-based inorganic-organic hybrids by using π-conjugated substituents as electron donors and stabilizers[J].Inorganic Chemistry,2013,52(3):1199-1205.
[23] WANG M S,XU G,ZHANG Z J,et al.Inorganic-organic hybrid photochromic materials[J].Chemical Communications,2010,46(3):361-376.
[24] ZENG Y,LIAO S J,DAI J C,et al.Fluorescent and photochromic bifunctional molecular switch based on a stable crystalline metal-viologen complex[J].Chemical Communications,2012,48(95):11641-11643.
[25] YANG X D,ZHU R,YIN J P,et al.Bipyridinium-bearing multi-stimuli responsive chromic material with high stability[J].Crystal Growth Design,2018,18(5):3236-3243.
[26] LI W B,YAO Q X,SUN L,et al.A viologen-based coordination polymer exhibiting high sensitivity towards various light sources[J].Cryst Eng Comm,2017,19(4):722-726.
[27] CHEN C,SUNJ K,ZHANG Y J,et al.Flexible viologen-based porous framework showing X-ray induced photochromism with single-crystal-to-single-crystal transformation[J].Angewandte Chemie-International Edition,2017,56(46):14458-14462.
[28] SUN J K,WANG P,YAO Q X,et al.Solvent- and anion-controlled photochromism of viologen-based metal–organic hybrid materials[J].Journal of Materials Chemistry,2012,22(24):12212-12219.
[29] ZHANG P P,YANG X D,SUN L,et al.The effect of different substituent groups of auxiliary ligands on the photochromic behaviors of bipyridinium-based coordination polymers[J].Inorganic Chemistry Communications,2017,75:8-11.
[30] LIU H,LV Y,LI S,et al.A solar ultraviolet sensor based on fluorescent polyoxometalate and viologen[J].Journal of Materials Chemistry C,2017,5(36):9383-9388.
[31] DESKA M,KOZLOWSKA J,SLIWA W.Rotaxanes and pseudorotaxanes with threads containing viologen units[J].Arkivoc,2013,SI(1):66-100.
[32] FREITAG M,GUNDLACH L,PIOTROWIAK P,et al.Fluorescence enhancement of di-p-tolyl viologen by complexation in Cucurbit[7]uril[J].Journal of the American Chemical Society,2012,134(7):3358-3366.
[33] YUAN T Y,VAZQUEZ M,GOLDNER A N,et al.Versatile thermochromic supramolecular materials based on competing charge transfer interactions[J].Advanced Functional Material,2016,26(47):8604-8612.
[34] MOGERA U,GEDDA M,GEORGE S J,et al.A supramolecular nanofiber-based passive memory device for remembering past humidity[J].Applied Materials & Interfaces,2017,9(37):32065-32070.
[35] ALOOTO P,GUAMIERI M,MORO F.Redox flow batteries for the storage of renewable energy:A review[J].Renewable & Sustainable Energy Review,2014,29:325-335.
[36] SOLOVEICHIK G L.Flow batteries:Current status and trends[J].Chemical Reviews,2015,115(20):11533-11558.
[37] DEBRULER C,HU B,MOSS J,et al.Designer two-electron storage viologen anolyte materials for neutral aqueous organic redox flow batteries[J].Chem,2017,3(6):961-978.
[38] HU B,DEBRULER C,RHODES Z,et al.Long-cycling aqueous organic redox flow battery(AORFB) toward sustainable and safe energy storage[J].Journal of the American Chemical Society,2017,139(3):1207-1214.
[39] LUO J,HU B,DEBRULER C,et al.A π-conjugation extended viologen as novel two-electron storage anolyte for total organic aqueous redox flow batteries[J].Angewandte Chemie-International Edition,2018,57(1):231-235.
[40] DEBRULER C,HU B,MOSS J,et al.A sulfonate-functionalized viologen enabling neutral cation exchange,aqueous organic redox flow batteries toward renewable energy storage[J].ACS Energy Letters,2018,3(3):663-668.
[2] MICHAELIS L,HILL E S.The viologen indicators[J].The Journal of General Physiology,1933,16(6):859-873.
[3] ALESANCO Y,VINUALES A,CABANERO G,et al.Colorless-to-black/gray electrochromic devices based on single 1-alkyl-1′-aryl asymmetric viologen-modified monolayered electrodes[J].Advanced Optical Materials,2017,5(8):1600989.
[4] KAN W Q,WEN S Z,HE Y C,et al.Viologen-based photochromic coordination polymers for inkless and erasable prints[J].Inorganic Chemistry,2017,56(24):14926-14935.
[5] SONG Y F,HUANG X H,HUA H J,et al.The synthesis of a rigid conjugated viologen and its cucurbituril pseudorotaxanes[J].Dyes and Pigments,2017,137:229-235.
[6] LIU T B,WEI X L,NIE Z M,et al.A Total organic aqueous redox flow battery employing a low cost and sustainable methyl viologen anolyte and 4-HO-TEMPO catholyte[J].Advanced Energy Materials,2016,6 (3):1501449.
[7] NANASAWA M,MIWA M,HIRAI M,et al.Synthesis of viologens with extended π-conjugation and their photochromic behavior on near-IR absorption[J].The Journal of Organic Chemistry,2000,65(2):593-495.
[8] CHEN G J,ZHOU Y,WANG X C,et al.Construction of porous cationic frameworks by crosslinking polyhedral oligomeric silsesquioxane units with N-heterocyclic linkers[J].Scientific Reports,2015,5:11236.
[9] DAS G,PRAKASAM T,NURYYEVA S,et al.Multifunctional redox-tuned viologen-based covalent organic polymers[J].Journal of Materials Chemistry A,2016,4 (40):15361-15369.
[10] Lü Z P,CHEN B,WANG H Y,et al.Charge-transfer supra-amphiphiles built by water-soluble tetrathiafulvalenes and viologen-containing amphiphiles:Supramolecular nanoassemblies with modifiable dimensions[J].Small,2015,11(29):3597-3605.
[11] ABOUELWAFA A S,MEREACRE V,BALABAN T S,et al.Photo- and thermally-enhanced charge separation in supramolecular viologen-hexacyanoferrate complexes[J].Crystengcomm,2010,12(1):94-99.
[12] SHI W,XING F F,BAI Y L,et al.High sensitivity viologen for a facile and versatile sensor of base an solvent polarity in solution and solid state in air atmosphere[J].ACS Applied Materials & Interfaces,2015,7(26):14493-14500.
[13] PARK S,KO H C,PAIK W,et al.Assignments of cyclic voltammetric peaks during electrochemical polymerization of pyrrole with viologen pendant[J].Synthetic Metals,2003,139(2):439-443.
[14] CHEN L,WILLCOCK H,WEDGE C J,et al.Efficient access to conjugated 4,4′-bipyridinium oligomers using the Zincke reaction:Synthesis,spectroscopic and electrochemical properties[J].Organic & Biomolecular Chemistry,2016,14(3):980-988.
[15] DURBEN S,BAUMGARTNER T.3,7-Diazadibenzophosphole oxide:A phosphorus-bridged viologen analogue with significantly lowered reduction threshold[J].Angewandte Chemie-International Edition,2011,50(34):7948-7952.
[16] WOODWARD A N,KOLESAR J M,HALL S R,et al.Thiazolothiazole fluorophores exhibiting strong fluorescence and viologen-like reversible electrochromism[J].Journal of the American Chemical Society,2017,139(25):8467-8473.
[17] MORTIMER R J.Electrochromic materials[J].Chemical Society Reviews,1997,26(3):147-156.
[18] BIRD C L,KUHN A T.Electrochemistry of the viologens[J].Chemical Society Reviews,1981,10(1):49-82.
[19] SYDAM R,GHOSH A,DEEPA M.Enhanced electrochromic write-erase efficiency ofa device with a novel viologen:1,1′-Bis(2-(1H-indol-3-yl)ethyl)-4,4′-bipyridinium diperchlorate[J].Organic Electronics,2015,17:33-43.
[20] PAN M J,KE Y L,MA L,et al.Single-layer electrochromic device based on hydroxyalkyl viologens with large contrast and high coloration efficiency[J].Electrochimica Acta,2018,266:395-403.
[21] ALESANCO Y,VINUALES A,PALENZUELA J,et al.Multicolor electrochromics:Rainbow-like devices[J].ACS Applied Materials & Interfaces,2016,8(23):14795-14801.
[22] LIN R G,XU G,WANG M S,et al.Improved photochromic properties on viologen-based inorganic-organic hybrids by using π-conjugated substituents as electron donors and stabilizers[J].Inorganic Chemistry,2013,52(3):1199-1205.
[23] WANG M S,XU G,ZHANG Z J,et al.Inorganic-organic hybrid photochromic materials[J].Chemical Communications,2010,46(3):361-376.
[24] ZENG Y,LIAO S J,DAI J C,et al.Fluorescent and photochromic bifunctional molecular switch based on a stable crystalline metal-viologen complex[J].Chemical Communications,2012,48(95):11641-11643.
[25] YANG X D,ZHU R,YIN J P,et al.Bipyridinium-bearing multi-stimuli responsive chromic material with high stability[J].Crystal Growth Design,2018,18(5):3236-3243.
[26] LI W B,YAO Q X,SUN L,et al.A viologen-based coordination polymer exhibiting high sensitivity towards various light sources[J].Cryst Eng Comm,2017,19(4):722-726.
[27] CHEN C,SUNJ K,ZHANG Y J,et al.Flexible viologen-based porous framework showing X-ray induced photochromism with single-crystal-to-single-crystal transformation[J].Angewandte Chemie-International Edition,2017,56(46):14458-14462.
[28] SUN J K,WANG P,YAO Q X,et al.Solvent- and anion-controlled photochromism of viologen-based metal–organic hybrid materials[J].Journal of Materials Chemistry,2012,22(24):12212-12219.
[29] ZHANG P P,YANG X D,SUN L,et al.The effect of different substituent groups of auxiliary ligands on the photochromic behaviors of bipyridinium-based coordination polymers[J].Inorganic Chemistry Communications,2017,75:8-11.
[30] LIU H,LV Y,LI S,et al.A solar ultraviolet sensor based on fluorescent polyoxometalate and viologen[J].Journal of Materials Chemistry C,2017,5(36):9383-9388.
[31] DESKA M,KOZLOWSKA J,SLIWA W.Rotaxanes and pseudorotaxanes with threads containing viologen units[J].Arkivoc,2013,SI(1):66-100.
[32] FREITAG M,GUNDLACH L,PIOTROWIAK P,et al.Fluorescence enhancement of di-p-tolyl viologen by complexation in Cucurbit[7]uril[J].Journal of the American Chemical Society,2012,134(7):3358-3366.
[33] YUAN T Y,VAZQUEZ M,GOLDNER A N,et al.Versatile thermochromic supramolecular materials based on competing charge transfer interactions[J].Advanced Functional Material,2016,26(47):8604-8612.
[34] MOGERA U,GEDDA M,GEORGE S J,et al.A supramolecular nanofiber-based passive memory device for remembering past humidity[J].Applied Materials & Interfaces,2017,9(37):32065-32070.
[35] ALOOTO P,GUAMIERI M,MORO F.Redox flow batteries for the storage of renewable energy:A review[J].Renewable & Sustainable Energy Review,2014,29:325-335.
[36] SOLOVEICHIK G L.Flow batteries:Current status and trends[J].Chemical Reviews,2015,115(20):11533-11558.
[37] DEBRULER C,HU B,MOSS J,et al.Designer two-electron storage viologen anolyte materials for neutral aqueous organic redox flow batteries[J].Chem,2017,3(6):961-978.
[38] HU B,DEBRULER C,RHODES Z,et al.Long-cycling aqueous organic redox flow battery(AORFB) toward sustainable and safe energy storage[J].Journal of the American Chemical Society,2017,139(3):1207-1214.
[39] LUO J,HU B,DEBRULER C,et al.A π-conjugation extended viologen as novel two-electron storage anolyte for total organic aqueous redox flow batteries[J].Angewandte Chemie-International Edition,2018,57(1):231-235.
[40] DEBRULER C,HU B,MOSS J,et al.A sulfonate-functionalized viologen enabling neutral cation exchange,aqueous organic redox flow batteries toward renewable energy storage[J].ACS Energy Letters,2018,3(3):663-668.